4-Hydroxybiphenyl → HCID 476768, compound

HRID 1828613Notes

Reaction equation

HRID 1828613 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanol

Product 1

HCID 476768HCID 476768, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 4 L three-necked round bottom flask fitted with a mechanical stirrer and a condenser were added 125.0 g of 4-hydroxybiphenyl (0.734 mol), 154.5 g of 6-bromo-1-hexanol (0.853 mol), 690 g of potassium carbonate, and 2500 ml of acetone. The reaction mixture was stirred and heated at reflux for 4 days and then filtered. The acetone was removed on a rotary evaporator, the residue was recrystallized from a mixture of ethyl acetate and hexanes to afford 188 g of white crystals (95%): mp 92–94° C.; 1H-NMR (CDCl3) δ (ppm) 1.30–1.84 (m, 8H), 3.65 (t, 2H), 3.99 (t, 2H), 6.98 (d, 2H), 7.32–7.56 (m, 7H).

Workup

  1. customTo a 4 L three-necked round bottom flask fitted with a mechanical stirrer and a condenser
  2. temperatureheated
  3. temperatureat reflux for 4 days
  4. filtrationfiltered
  5. customThe acetone was removed on a rotary evaporator
  6. customthe residue was recrystallized from a mixture of ethyl acetate and hexanes

Sources & evidence

ORD record
ord-2f06b02de9df48b79998d0870a1b1d6e
Source dataset
uspto-grants-2006_06
Patent number
US07058249B2

Reaction notes

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